Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Unsaturated cyclic and acyclic carbamates exhibiting taste and flavor enhancement effect in flavor compositions

Active Publication Date: 2007-06-14
INTERNATIONAL FLAVORS & FRAGRANCES
View PDF15 Cites 25 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0024] In addition to the novel compounds and the use of the compounds to enhance the taste of foodstuffs by the i

Problems solved by technology

MSG is the most widely used material as a ‘taste enhancer’ where it synergizes the perception of ‘savory’ ingredients, but has also been alleged to cause allergic reaction to a proportion of the population.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Unsaturated cyclic and acyclic carbamates exhibiting taste and flavor enhancement effect in flavor compositions
  • Unsaturated cyclic and acyclic carbamates exhibiting taste and flavor enhancement effect in flavor compositions
  • Unsaturated cyclic and acyclic carbamates exhibiting taste and flavor enhancement effect in flavor compositions

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of Materials of the Present Invention

[0078] The following reaction sequence was used to prepare the specific compounds described by the NMR data set forth below:

[0079] The amine and triethylamine were dissolved in dichloromethane or ethyl acetate to which the corresponding chloroformate was added in 1.0 to 2.0 equivalents at temperatures ranging from 0° C. to room temperature, most preferably from 5° C. to 15° C. The resulting solution was aged for about 1-3 hours at room temperature.

[0080] The reaction was quenched with aqueous sodium chloride, hydrogen chloride or sodium hydroxide depending upon the need to remove residual acid or amine. The mixture was extracted into ethereal solvent or dichloromethane, washed to neutrality and solvent removed.

[0081] The crude product was purified by distillation or recrystallization depending on the physical properties.

[0082] The carbamates were synthesized according to the general scheme above with the following specific examp...

example ii

[0098] The following reaction sequence was used to make the compound described by the NMR data set forth below:

[0099] Corey's cyclopropanation of compound I, a chemical that is commercially known as Citralva, gives rise to compound II in good yield. The above mentioned transformation proceeds via the trimethylsulfoxium ylide which is generated in-situ from the reaction of trimethylsulfoxium iodide, (CH3)3SOI, and sodium hydride in dimethylsulfoxide, DMSO. Next, metal hydride reduction of compound II affords compound III quantitatively.

Ethyl ([2-methyl-2-(4-methylpent-3-en-1-yl)cyclopropyl]methy)carbamate

[0100] 1-[2-methyl-2-(4-methylpent-3-en-1-yl)cyclopropyl]methanamine (20.0 g, 0.12 mol)in 150 mL of ethyl acetate and ethylchloroformate (17.9 g, 0.165 mol) were charged to a reaction flask. The reaction mixture was then cooled to 0° C. Triethylamine (23.8 g, 0.165 mol) was slowly added while maintaining the reaction temperature at 0° C. Once the feed was complete the reaction mi...

example iii

[0101] The following reaction sequence was used to make the compound described by the NMR data set forth below:

Ethyl (2-[(3Z)-hex-3-en-1-yl]cyclopropyl)methyl)carbamate

[0102] Compound IV is a commercially available starting material (AVAILABLE from Bedoukian Research). The conversion of IV to V is a known transformation, which proceeds via an oxime intermediate. Subsequent transformations to the final product follow a similar synthetic scheme to that of example II 1-(2-[(3Z)-hex-3-en-1-yl]cyclopropyl)methanamine 1 eq 1.4 eq of ethylchloroformate, 1.4 eq of triethylamine, quenched with saturated sodium chloride solution, 70% yield. 1H NMR (500 MHz, CDCl3) δ: −0.12 −0.63 (m, 2H), 0.67-0.74 (m, 1H), 0.81-0.88 & 0.95-0.99 (m, 1H), 0.96 (td, J=7.53, 1.09 Hz, 3H), 1.18-1.29 & 1.44-1.51 (m, 1H), 1.24 (t, J=7.06 Hz, 3H), 1.30-1.39 (m, 1H), 1.98-2.08 (m, 2H), 2.09-2.17 (m, 2H), 3.01-3.05 (m, 1H), 3.11-3.24 (m, 1H), 4.11 (q, J+6.50 Hz, 2H), 4.60-4.77 (br.s, 1H), 5.31-5.47 (m, 2H)

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Fractionaaaaaaaaaa
Fractionaaaaaaaaaa
Percent by massaaaaaaaaaa
Login to View More

Abstract

The present invention relates to novel compounds having sweet, salt or umami taste enhancement qualities. These compounds have the structure: where R1 is H or methyl; R2 is selected from the group consisting of H, C1-C4 alkyl, alkenyl; R3 is selected from the group consisting of H, phenyl, C1-C10 straight or branched chain alkyl, alkenyl, alkynyl, alkyldienyl, acyclic or containing no more than one ring, which contains no more than a total of five heteroatoms selected from F, O, S, N, and P; and if R1=H, R2 and R3 taken together can represent cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl, which contains no more than two of each heteroatom selected from N, O, and S; or if R1, R2 and R3 taken together can represent one, or two aromatic rings, which contain no more than three of each heteroatom selected from F, N, S, and O. R4 is selected from the group consisting of H, methyl or ethyl; R5 is selected from the group consisting of H, methyl and ethyl; R6 is selected from the group consisting of H, C1-C9 straight or branched chain alkyl, alkenyl, alkyldienyl, acyclic or containing no more than one ring; except for in the case of structure 1 when if R4=H or methyl and R5=H or methyl, R6 as described above and phenyl; or when R4, R5, and R6 taken together can be equal to R7 is selected from the group consisting C1-C4 alkyl, or alkenyl.

Description

FIELD OF THE INVENTION [0001] Unsaturated cyclic and acyclic carbamate compounds having sweet, salt or umami taste and flavor enhancement quality. BACKGROUND OF THE INVENTION [0002] The term Umami, from the Japanese word to describe savory or meaty, is the term used to describe the unique overall fullness, savory or salivatory taste of food. Materials that exhibit this taste quality generally potentiate the intensity of glutamate solutions and this is one important characteristic of umami taste. It is increasingly becoming recognized as the fifth sense of taste, the others being sour, sweet, salt and bitter. Compounds traditionally described as possessing this character are monosodium glutamate (MSG), protein hydrolysates, some amino acids and certain nucleotides and phosphates. [0003] MSG is the most widely used material as a ‘taste enhancer’ where it synergizes the perception of ‘savory’ ingredients, but has also been alleged to cause allergic reaction to a proportion of the popul...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): A23L1/236A23L27/00A23L27/20A23L27/30
CPCA23L1/226C07C271/12C07C271/34C07C271/44C07C317/18C07C333/04C07C2101/02C07C2101/08C07C2101/14C07C2101/16C07D333/48A23L27/20C07C2601/02C07C2601/08C07C2601/14C07C2601/16
Inventor PEI, TAODEWIS, MARK L.JANCZUK, ADAM JAN
Owner INTERNATIONAL FLAVORS & FRAGRANCES
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com